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ε-カプロラクトン

epsilon-CAPROLACTONE

HCID 10401
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
502-44-3
標準SMILES
O=C1CCCCCO1
InChIKey
PAPBSGBWRJIAAV-UHFFFAOYSA-N
分子式
C6H10O2
平均分子量
114.14 g/mol
単同位体質量
114.06807956

概要

Hexano-6-lactone is a -lactone that is oxepane substituted by an oxo group at position 2.

名称と識別子

優先名称
epsilon-CAPROLACTONE
IUPAC
oxepan-2-one
現地名
ε-カプロラクトン
英語名
ε-Caprolactone
分子式
C6H10O2
分子量
114.14

名称と別名

Epsilon-caprolactoneCAPROLACTONE502-44-36-Hexanolactone2-Oxepanonehexano-6-lactone6-Hexanolide1,6-Hexanolide1-Oxa-2-oxocycloheptanePlaccel M6-Hydroxyhexanoic acid lactoneHexanoic acid, epsilon-lactone
名称をさらに表示
ε-カプロラクトンΕ-カプロラクトン(モノマー)2-オキセパノンεカプロラクトンε-ヘキサノラクトンε-ヘキサラクトンΕ‐カプロラクトン(モノマー)6-ヘキサノリド^Ε-カプロラクトン6-ヘキサノラクトン^ε-カプロラクトン, 99%oxepan-2-oneOxepanoneE-CAPROLACTONEPolycaprolactone Polyol6-CAPROLACTONE6-Hydroxyhexan-6-olide
Hexamethylene oxide, 2-oxo-epsilon-KaprolaktonDTXSID4027159epsilon caprolactoneCHEBI:17915TONE ECEQHexanoic acid, 6-hydroxy-, epsilon-lactone56RE988L1R

データベース識別子

CAS
502-44-3
PubChem CID
10401
DTXSID
DTXSID4027159
ChEMBL
CHEMBL373123
ChEBI
CHEBI:17915
UNII
56RE988L1R
EC Number
207-938-1
Nikkaji
J1.566K

物性

構造計算による物性補完中

XLogP
0
極性表面積
26.3 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
0
重原子数
8
形式電荷
0
複雑度
88.5

実験および物理化学的性質

Chemical ClassesOther Classes -> Lactones
SpringerMaterials PropertiesCoriolis coupling
LogP · 2 件

log Kow= 1.215 (calc)

0.68

Density · 3 件

1.07 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.00

1.0761 @ 20°C

SolubilitySolubility in water: miscible
Flash Point127 °C o.c.
Boiling Point · 2 件

237 °C

215 °C @760 [mm Hg]

Melting Point · 2 件

-1.5 °C

-1 °C

Vapor DensityRelative vapor density (air = 1): 3.9
Vapor Pressure · 4 件

0.13 [mmHg]

1.35X10-1 mm Hg at 25 °C

Vapor pressure, Pa at 25 °C: 0.8

0.01 [mm Hg] @20 °C

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 34.5% (266 of 770) of reports.

Warning

H319 (60.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 770 reports by companies from 8 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 5 件

Chemical: 2-Oxepanone

Council Directive (EEC) No 109/1989 (Repealed by Reg. EC No 1935/2004 (amended))

2-Oxepanone is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Oxepanone are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 07-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14740

Caprolactone: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsCombustible.
Hazards Summary · 1 件

Emergency treatment: irritants; [HSDB] Rapidly hydrolyzed in the body to 6-hydroxyhexanoic acid and rapidly excreted in urine; Irritating to eyes; No adverse effects in a 9-day inhalation study at 45 ppm; No evidence of reproductive effects; [ToxPlanet: UNEP: SIDS] An irritant; [MSDSonline]

Chemical DangersReacts with strong bases, strong acids and strong oxidants.
Hazard Classes and CategoriesEye Irrit. 2A (60.1%)
Explosive Limits and PotentialExplosive limits , vol% in air: 1.2-9

化学と産業

薬理情報

Mechanism of ActionCAPROLACTONE INHIBITED PROTEOLYTIC & FIBRINOLYTIC ACTIVITIES OF HUMAN PLASMIN. IN VERY LOW CONCN, IT ALSO INHIBITED ACTIVATION OF PLASMINOGEN THROUGH PLASMIN-STREPTOKINASE ACTIVATOR & HUMAN UROKINASE.

用途と製造

Uses · 3 件

Used as a solvent, a diluent for epoxy resins, and an intermediate in adhesives, urethane coatings, and elastomers; [Hawley] Used in the production of polymers (polycaprolactones); [eChemPortal: SIDSUNEP]

Plastic Composites Manufacturing [Category: Industry]

INTERMEDIATE IN ADHESIVES, URETHANE COATINGS & ELASTOMERS; SOLVENT; DILUENT FOR EPOXY RESINS; SYNTHETIC FIBERS; IN ORG SYNTHESIS

U.S. Imports(1983) 4.30X10+8 g /4-Caprolactone/
U.S. Production2023: 10,000,000 - <25,000,000 lb
Industry UsesMonomers
Methods of ManufacturingREACTION PRODUCT OF PERACETIC ACID & CYCLOHEXANONE; AN INTERMEDIATE PRODUCT IN MFR OF CAPROLACTAM.
General Manufacturing Information · 2 件

Paint and Coating Manufacturing

2-Oxepanone: ACTIVE

応用分野 · 4 件

用途ウレタンの原料、高分子ポリエステル原料、樹脂改質剤。

用途ε-カプロラクトンはその大部分がε-カプロラクタムの原料として消費される[3]。また、高度に特殊化したポリマーのモノマーとしても用いられる。開環重合させるとポリカプロラクトン(PCL)が生成する。

使用ε-Caprolactone is widely used as a monomer in the manufacturing of highly specialized polymers. It is mainly utilized as a precursor to caprolactam. It finds an application in the synthesis of polyglecaprone, which is used as a suture material in surgery.

関連反応

212 件
反応記録を作成
HRID 2257 の反応式
HRID 2257反応物としてuspto-grants-1998_03
HRID 2260 の反応式
HRID 2260反応物としてuspto-grants-1998_03
HRID 2261 の反応式
HRID 2261反応物としてuspto-grants-1998_03
HRID 2262 の反応式
HRID 2262反応物としてuspto-grants-1998_03
HRID 2263 の反応式
HRID 2263反応物としてuspto-grants-1998_03
HRID 2264 の反応式
HRID 2264反応物としてuspto-grants-1998_03
HRID 2265 の反応式
HRID 2265反応物としてuspto-grants-1998_03
HRID 2969 の反応式
HRID 2969反応物としてuspto-grants-1998_03
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化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
Food Contact Substances
FCS -> FDA Cumulative Estimated Daily Intake (CEDI)
Physical Description · 3 件

CBI; Liquid

Colorless liquid; Miscible in water; [eChemPortal: SIDSUNEP] Colorless liquid; [MSDSonline]

COLOURLESS HYGROSCOPIC LIQUID WITH CHARACTERISTIC ODOUR.

物理化学的性質

融点
-1 °C · -1 °C
沸点
96 · 96-97.5 °C10 mm Hg(lit.)
比重(密度)
1.03 g/mL · 1.03 g/mL at 25 °C(lit.)
蒸気密度
3.9 · 3.9 (vs air)
蒸気圧
0.01 mm · 0.01 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.463(lit.)
闪点
229 °F · 229 °F
貯蔵温度
30 °C · Store below +30°C.
溶解性
クロロホルム、酢酸エチル
外見
液体
色
無色透明、経年黄変
爆発限界(explosive limit)
1.2 · 1.2-9%(V)
水溶解度
1000 MG/L · >1000 MG/L (20℃)
BRN
106919 · 106919
Henry's Law Constant
5.5 · 5.5×10-2 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
1S/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2
InChIKey
PAPBSGBWRJIAAV-UHFFFAOYSA-N
SMILES
O=C1CCCCCO1
LogP
0.32 at · 0.32 at 20℃
CAS データベース
502 · 502-44-3(CAS DataBase Reference)
NISTの化学物質情報
2 · 2-Oxepanone(502-44-3)
EPAの化学物質情報
2 · 2-Oxepanone (502-44-3)

化学的性質

化学的特性Clear colorless liquid, yellowing on ageing

安全と保護具

Fire FightingUse powder, alcohol-resistant foam, water spray, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures · 4 件

Fresh air, rest.

Rinse skin with plenty of water or shower.

Rinse with plenty of water (remove contact lenses if easily possible). Refer for medical attention.

Rinse mouth.

Safe StorageSeparated from strong bases, strong acids and strong oxidants. Dry. Well closed.
Spillage DisposalPersonal protection: safety goggles. Collect leaking liquid in covered containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Eye PreventionWear safety goggles.
Fire PreventionNO open flames.
Inhalation RiskEvaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly on spraying.
Skin PreventionProtective gloves.
Ingestion PreventionDo not eat, drink, or smoke during work.
Inhalation PreventionUse ventilation.
Effects of Short Term ExposureThe substance is irritating to the eyes.
Protective Action Criteria (PAC) · 3 件

13 [mg/m3]

140 [mg/m3]

850 [mg/m3]

毒性情報

Environmental Fate · 3 件

TERRESTRIAL FATE: There are no biodegradation studies in soil to indicate whether biodegradation of caprolactone may be significant. An estimated Koc value of 109.1(1) suggests high mobility in soil(2,SRC).

AQUATIC FATE: Volatilization half-lives for caprolactone of 0.35 and 3.9 days have been estimated for a model river (one meter deep) and a model environmental pond, respectively(1-2). An estimated Koc of 109.1 and BCF of 4.94 for caprolactone indicate that adsorption to sediment and bioconcentration in aquatic organisms are not important fate processes(1). No information on biodegradation of caprolactone was available(SRC).

ATMOSPHERIC FATE: Based on a measured vapor pressure of 1.35X10-1 mm Hg at 25 °C(1), caprolactone can be expected to exist almost entirely in the vapor-phase in the ambient atmosphere(SRC). Vapor-phase caprolactone is degraded slowly in the ambient atmosphere by reaction with photochemically formed hydroxyl radicals; the half-life for this reaction in air can be estimated to be about 2.76 days(2,SRC).

Signs and SymptomsRedness. Pain.
Effluent ConcentrationsCaprolactone was qualitatively identified in advanced waste water treatment concentrates from Pomona, CA(1-2).
Soil Adsorption/MobilityBased on a calculated log Kow of 1.215(1), the Koc for caprolactone can be estimated to be approximately 109.1(2,SRC). This Koc value indicates that caprolactone has high mobility in soil(3).
Human Toxicity Excerpts · 1 件

The efficacy, safety and patient acceptance of a subcutaneous implant of levonorgestrel contained in a biodegradable capsule of poly (E-caprolactone) wax are reported in 48 women, aged 18-40 yr, 32 of whom were given an implant containing a 21.6 mg dose of levonorgestrel, and 16 were initially given an implant containing 12 mg of levonorgestrel; patients were followed up for one yr. Ovulation occurred in all cycles in patients given the 12 mg dose, and in 26.3% of cycles in the group given 21.6 mg. Levonorgestrel blood levels were significantly lower in those given 12 mg. All patients initially given 12 mg were given a second implant of the same dose. Bleeding patterns were regular in most women who ovulated and irregular in most remaining subjects. It was assumed that changes in cervical mucus and the endometrium contributed to effective contraception despite the frequency of ovulation.

Artificial Pollution SourcesAs a reaction product of peracetic acid and cyclohexanone(1) and during its use as an intermediate or diluent(1), caprolactone may be released to the environment as emissions or in waste streams(SRC).
Environmental Bioconcentration · 1 件

Based on a calculated log Kow of 1.215(1), the BCF for caprolactone can be estimated to be 4.94 using a recommended regression derived equation(2,SRC). This BCF value indicates that bioconcentration of caprolactone in aquatic organisms is not significant(SRC).

Volatilization from Water/Soil · 1 件

The Henry's Law constant for caprolactone can be estimated to be 1.809X10-4 atm-cu m/mole at 25 °C(1,SRC). Using this value of Henry's Law constant, one estimates that the volatilization half-life of caprolactone from a model river 1 m deep flowing 1 m/sec with a wind velocity of 3 m/sec has been estimated to be approximately 0.35 days(2,SRC). The volatilization half-life of caprolactone from a model environmental pond can be estimated to be approximately 3.9 days(3,SRC).

Non-Human Toxicity Excerpts · 2 件

THE MUTAGENIC ACTIVITES OF 79 CARCINOGENS, NONCARCINOGENS, & STRUCTURALLY RELATED CMPD TOWARD SALMONELLA TYPHIMURIUM & SACCHAROMYCES CEREVISIAE D3 STRAINS WERE INVESTIGATED IN THE IP HOST-MEDIATED ASSAY. EPSILON-CAPROLACTONE WAS NOT MUTAGENIC TOWARD SALMONELLA TYPHIMURIUM STRAINS TA1530 OR TA1535 IN THE HOST-MEDIATED ASSAY, AND DID NOT INCREASE MITOTIC RECOMBINATION IN SACCHAROMYCES CEREVISIAE D3.

OF 13 DIRECT-ACTING ALKYLATING AGENTS, ONLY ONE NONCARCINOGEN, EPSILON-CAPROLACTONE, WAS TESTED IN THE SYRIAN HAMSTER EMBRYO CELL TRANSFORMATION SYSTEM, & IT YIELDED NEGATIVE RESULTS IN BOTH IN VITRO SYSTEMS.

Environmental Abiotic Degradation · 1 件

The rate constant for the vapor-phase reaction of caprolactone with photochemically produced hydroxyl radicals has been estimated to be 5.81X10-12 cu cm/molecule-sec at 25 °C(1) which corresponds to an atmospheric half-life of about 2.76 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).

Probable Routes of Human ExposureIn occupational settings, exposure to caprolactone may occur through inhalation of vapors and through eye and skin contact. (SRC)
Environmental Fate/Exposure Summary · 1 件

Caprolactone may be released to the environment during its use as an intermediate in the manufacture of caprolactam, adhesives, urethane coatings and elastomers, solvents, synthetic fibers, as a diluent for epoxy resins, during organic synthesis, and as a reaction product of peracetic acid and cyclohexanone. If released to the atmosphere, caprolactone is degraded slowly by reaction with photochemically produced hydroxyl radicals (estimated half-life of 2.76 days in air). A calculated Koc value of 109.1 suggests a high mobility of caprolactone in soil. A calculated BCF of 4.94 for caprolactone indicates that its bioconcentration in aquatic organisms should not be important. Based on a calculated Henry's Law constant of 1.809X10-4 atm cu-m/mole at 25 °C, and half-lives of 3.9 and 0.35 days from a model environmental pond and a model river, respectively, caprolactone is expected to volatilize rapidly from water. In occupational settings, exposure to caprolactone may occur through inhalation of vapors and through eye and skin contact. (SRC)

安全データ

wgk
2
tsca
TSCA listed
rtecs
MO8400000
毒性
LD50 orally in Rabbit: > 2000 mg/kg LD50 dermal Rabbit 5990 mg/kg
hs_code
29322090
risk_code
37/38-41-36/38
化審法
(5)-1091
消防法
危-4-3-III
hazard_code
Xi
safety_code
26-39-37/39
自然発火温度
204 °C
Hazard Classifications
Eye Irrit. 2
ストレージクラス
10 - Combustible liquids
有毒物質データの
502-44-3(Hazardous Substances Data)

一般的な説明ε-caprolactone is a cyclic ester. Ring opening polymerization of ε-caprolactone initiated by, tributylin n butoxide, ethyl magnesium bromide, or samarium acetate or heteropolyacid, leads to the formation of poly caprolactone (PCL).

上流・下流製品情報

上流原料

エタンペルオキシ酸オゾンシクロヘキサノン7,8,15,16-テトラオキサジスピロ[5.2.5.2]ヘキサデカン6-ヒドロキシカプロン酸

下流製品

(5-カルボキシペンチル)トリフェニルホスホニウムブロマイド 臭化物 リン6-ヒドロキシヘキサン酸TERT-ブチル6-クロロカプロン酸クロリド6-オキソヘキサン酸メチル8-フルオロ-3-メチルオクタン酸

補足説明

定義ChEBI: A epsilon-lactone that is oxepane substituted by an oxo group at position 2.